Hydrochloric Acid → (6-Amino-2,3-dichlorophenyl)methanol

HRID 614900Notes

Reaction equation

HRID 614900 reaction equation
B.[Cl:2][C:3]1[C:11]([Cl:12])=[C:7]([C:8](O)=[O:9])[C:6]([NH2:13])=[CH:5][CH:4]=1.Cl>O1CCCC1>[NH2:13][C:6]1[C:7]([CH2:8][OH:9])=[C:11]([Cl:12])[C:3]([Cl:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 121045466-Amino-2,3-dichlorobenzoic acid

Product 1

HCID 14998901(6-Amino-2,3-dichlorophenyl)methanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane (0.55 mol) in 550 ml of tetrahydrofuran was slowly added, over a period of 1 hour, to a solution of 5,6-dichloroanthranilic acid (44.5 g, 0.216 mol) in tetrahydrofuran (1200 ml). The solution was heated at reflux for 18 hours, cooled and treated slowly with 550 ml of 1N HCl. The tetrahydrofuran was removed in vacuo at 30° and the aqueous mixture was washed with ether and then made basic with concentrated NH4OH. The resulting solid was extracted with ether, dried (K2CO3) and the solvent was evaporated to leave 31.5 g. (76%) of the title compound as light pinkish needles, m.p. 133.5°-135°. An analytical sample was prepared by recrystallization from benzene; white needles, m.p. 134°-135.5°.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 18 hours
  3. temperaturecooled
  4. customThe tetrahydrofuran was removed in vacuo at 30°
  5. washthe aqueous mixture was washed with ether
  6. extractionThe resulting solid was extracted with ether
  7. dry with materialdried (K2CO3)
  8. customthe solvent was evaporated
  9. customto leave 31.5 g

Sources & evidence

ORD record
ord-8b3969a9c4c349379f2187311877c752
Source dataset
uspto-grants-1979_03
Patent number
US04146718

Reaction notes

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